No

You decide against telling her about your sexual romps. It's not like she doesn't already know you like crossdressing. In fact she thinks you're kind of cute as a girl. But you think it would be wrong.

You work until the work day is over and head into your boss's office. You enter her office quietly and she's on he computer typing away. She motions you to sit and ignores you for what seems like an eternity. You bite your lip as your mind starts to wander to her thick member. You begin to daydream and snap to when she turns to face you. You notice she has a small pair of keys on the desk, clearly to your cage. She taps her nails on the desk and stares at you impatiently. You sit there oblivious. "Well hurry up and get out of that horrid uniform. I swear it's like you can't take a hint." You begin immediately stripping down to your panties and blush. She grabs the cage to see your small penis trying it's best to fight against the unforgiving hard plastic. She taps it a bit and inspects it grinning at your discomfort.

"Now I want you to dress in something that really suits you tomorrow. You know like a sissy. You are to wear it under your current uniform. Dismissed." You stand there wondering when she will remove this chastity cage. You open your mouth but she interrupts you, "I said dismissed, that means get dressed and leave mr.Pecker." You get dressed and head home